You put this so well. I think part of what makes us uneasy is that somehow we feel that we're not being genuine if we do give things forethought--and yet that's not necessarily true at all. As you say, some people can accomplish self-management without giving it a thought at all, whereas other people do think about it. And good point also about the person who can't read social cues.

I think thinking about it can mean healthy self-awareness (thought maybe too much thinking about it can be unhealthy hyperawareness---but a lot depends on the person).

This is tangential, but: one thing I've noticed, very definitely, is that my sense of online interactions and what I feel comfortable with is constantly evolving. My impressions of things have changed as I've been online longer.